After leaving Dan for not taking better care of himself, Roseanne goes on a "spiritual odyssey", imagining herself and Dan as Ann and Donald from "That Girl", Jeannie and Major Nelson from "I Dream of Jeannie", and Mary and Lou from "The Mary Tylor Moore Show". The family tries console Dan, and encourage Roseanne to reconcile with her heart-broken husband. Jackie discovers that they won the Illinois State Lottery worth 108 million dollars.
After finding out they won the Illinois State Lottery, the Conners and family imagine how to spend their new-found wealth. Kathleen Sullivan and Robin Leach interview Dan and Roseanne in their home. Throwing a party in their home proves that people really do come out of the woodwork to help celebrate wealth. Dan and Roseanne vow to not let money change who they are.
While sitting around the dinner table with her family, talking about their lottery winnings, Roseanne daydreams about herself and the family being on "Jerry Springer Show, The" (1991), she and Jackie posing for "Playboy", and winning the Miss Universe contest.
Jackie and Roseanne plan an expensive spa vacation. Depressed about his mother, Dan searches for the meaning of life. He decides that now that he can afford it, he wants to take her to California for a thorough evaluation of her psychiatric condition. The crowned Prince of Muldavia sees Jackie on TV and decides he must go to Lanford to meet her.
The Conners get a taste of upper crust living when they visit the wealthy Wentworth family at their home on Martha's Vineyard. The experience proves eye-opening when the Conner family discovers the pill-popping, alcohol-sipping, and irresponsibility of Astrid's dysfunctional family. As the weekend drags on, the Conners give the Wentworths a lesson in real life.
Thanksgiving for the Conners starts on a sour note with the news Dan won't be able to make it home for the holiday. However, Roseanne is thrilled she can afford to have the meal catered instead of spending an entire day in the kitchen. Family squabbles combined with a shocking revelation by Bev nearly ruins the evening. The family must contend with the fact that money does not necessarily buy happiness.
Dan finally returns home after a long stay in California with his ill mother. He, Roseanne, and the entire family realize how much they have to be thankful for as one of the oddest and most trying years of their lives comes to an end. The only problem is how distant and uncomfortable Dan seems to be around Roseanne.
When Roseanne falls into a deep depression and locks herself in the bedroom, family and friends try their hardest to pick her spirits back up. When their efforts prove fruitless, they stage an intervention to rouse a lethargic Roseanne out of bed.
Roseanne makes a surprising connection with Edgar Wellman Jr., the son of her hated former boss, at a Lanford Country Club party. When he reveals some awful news about the future of Lanford, Roseanne may be the only one who can save her hometown.
Dan is unnerved by rumors of Roseanne and Edgar so he makes a surprise trip to see her. They make some tentative steps to putting the pieces of their marriage back together. Their peace in interrupted when a frantic call comes in from Jackie: Darlene has unexpectedly been rushed to the hospital.
Darlene gives birth to a very premature baby girl. The doctors and specialists have very little hope for the baby's survival. The family is crushed but Roseanne is determined to prove pure love, affection, and a tender touch are more powerful than any medicine.
The Conners are approached by different network and cable film developers, each hoping to get the right to their "rags to riches" story. What starts out as excitement and enthusiasm for the family, soon dims when they realize that none of the producers they interview with wants to portray them as they really are. A tabloid reporter approaches Beverly, Joan and Leon for stories about Roseanne and her family, and they are only too eager to dish the dirt.
The Conners welcome baby Harris Conner-Healy home. Roseanne is delighted Darlene wants to live at home and work on her parenting skills. The family talks about their lives after winning the lottery and are glad they have all come out of it stronger people. Over a pizza dinner, Roseanne suggests they say grace to thank God that Harris survived and the family is together again.
Family and friends gather at the Conner house to celebrate baby Harris' Homecoming and everyone takes a turn chatting with the new addition to the family. Mark and Becky have some exciting news, as do Leon and his husband Scott. During dinner, Roseanne takes time to reflect on each member of her family and reveals she has been writing a book; everything we see is Roseanne's altered version of actual events. Roseanne reveals the true story and admits she changed whatever details she didn't like about her life and the people in it. In truth, the Conners never won the ...